ATE527372T1 - SELECTIVE ENZYMATIC ESTERIFICATION AND SOLVOLYSIS OF AN EPIMERIC VITAMIN D ANALOG AND SEPARATION OF THE EPIMERS - Google Patents

SELECTIVE ENZYMATIC ESTERIFICATION AND SOLVOLYSIS OF AN EPIMERIC VITAMIN D ANALOG AND SEPARATION OF THE EPIMERS

Info

Publication number
ATE527372T1
ATE527372T1 AT03729607T AT03729607T ATE527372T1 AT E527372 T1 ATE527372 T1 AT E527372T1 AT 03729607 T AT03729607 T AT 03729607T AT 03729607 T AT03729607 T AT 03729607T AT E527372 T1 ATE527372 T1 AT E527372T1
Authority
AT
Austria
Prior art keywords
epimers
analog
solvolysis
separation
enzymatic esterification
Prior art date
Application number
AT03729607T
Other languages
German (de)
Inventor
Evgeny Shapiro
Ayelet Fishman
Reinhard Effenberger
Asher Maymon
Anchel Schwartz
Original Assignee
Teva Pharma
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Teva Pharma filed Critical Teva Pharma
Application granted granted Critical
Publication of ATE527372T1 publication Critical patent/ATE527372T1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/62—Carboxylic acid esters
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy group
    • C12P7/04—Preparation of oxygen-containing organic compounds containing a hydroxy group acyclic
    • C12P7/18—Preparation of oxygen-containing organic compounds containing a hydroxy group acyclic polyhydric
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/0004—Oxidoreductases (1.)
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
    • C12P41/003—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions
    • C12P41/004—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions by esterification of alcohol- or thiol groups in the enantiomers or the inverse reaction

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • General Engineering & Computer Science (AREA)
  • Microbiology (AREA)
  • Biotechnology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Analytical Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Biomedical Technology (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Abstract

Provided is a method of selectively enzymatically esterifying or selectively enzymatically solvolyzing epimers of analogs of vitamin D having a stereogenic center at C-24 that has a free or esterified OH group. The metod can be used, for example, for separating mixed epimers of the vitamin D analog.
AT03729607T 2002-01-10 2003-01-09 SELECTIVE ENZYMATIC ESTERIFICATION AND SOLVOLYSIS OF AN EPIMERIC VITAMIN D ANALOG AND SEPARATION OF THE EPIMERS ATE527372T1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US34808202P 2002-01-10 2002-01-10
US34997702P 2002-01-18 2002-01-18
PCT/US2003/000623 WO2003060094A2 (en) 2002-01-10 2003-01-09 Selective enzymatic esterification and solvolysis of epimeric vitamin d analog and separation of the epimers

Publications (1)

Publication Number Publication Date
ATE527372T1 true ATE527372T1 (en) 2011-10-15

Family

ID=26995556

Family Applications (1)

Application Number Title Priority Date Filing Date
AT03729607T ATE527372T1 (en) 2002-01-10 2003-01-09 SELECTIVE ENZYMATIC ESTERIFICATION AND SOLVOLYSIS OF AN EPIMERIC VITAMIN D ANALOG AND SEPARATION OF THE EPIMERS

Country Status (15)

Country Link
US (1) US8129173B2 (en)
EP (1) EP1470220B1 (en)
JP (1) JP2005514929A (en)
KR (1) KR100630859B1 (en)
CN (1) CN1639329A (en)
AT (1) ATE527372T1 (en)
AU (1) AU2003210473A1 (en)
CA (1) CA2472178A1 (en)
HR (1) HRP20040674A2 (en)
IL (1) IL162920A0 (en)
IS (1) IS7347A (en)
MX (1) MXPA04006741A (en)
NO (1) NO20043323L (en)
PL (1) PL373677A1 (en)
WO (1) WO2003060094A2 (en)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8263580B2 (en) * 1998-09-11 2012-09-11 Stiefel Research Australia Pty Ltd Vitamin formulation
AU2003275987A1 (en) 2002-06-13 2003-12-31 Teva Pharmaceutical Industries Ltd. Epimerization of analogs of vitamin d
US7351869B2 (en) 2002-11-18 2008-04-01 Teva Pharmaceutical Industries Ltd Crystallization method for purification of calcipotriene
US8362287B2 (en) 2004-03-18 2013-01-29 Leo Pharma A/S Stereoselective synthesis of vitamin D analogues
PL207034B1 (en) 2004-12-30 2010-10-29 Inst Farmaceutyczny Method for the manufacture of anhydrous calcipotriol
EP2526930B1 (en) 2005-06-01 2013-12-25 GlaxoSmithKline Intellectual Property Development Limited Vitamin formulation
TW200643172A (en) * 2005-06-01 2006-12-16 Formosa Lab Inc Selective enzymatic esterfication and solvolysis of epimeric vitamin D analog and separation and epimerization of the epimers
CN100404686C (en) * 2005-06-10 2008-07-23 台耀化学股份有限公司 Method for separating and isomerizing vitamin D derivative isomer
CN101906443B (en) * 2010-06-25 2012-07-25 绍兴文理学院 Synthesis method of (2S)-[2-(t-tertiary butyl)dimethylsilioxy]-2-cyclopropyl-1-ethyl-triphenylphosphine
US9119528B2 (en) 2012-10-30 2015-09-01 Dexcom, Inc. Systems and methods for providing sensitive and specific alarms
CN103694156B (en) * 2014-01-07 2015-09-02 成都医路康医学技术服务有限公司 A kind of preparation method of curing psoriasis medicine calcipotriol
CN104830943B (en) * 2015-03-18 2019-03-01 上海皓元生物医药科技有限公司 A kind of preparation method of Ai Er ossification alcohol intermediate
CN106188122B (en) * 2015-05-05 2019-05-14 上海医药工业研究院 A kind of epimerization method of chiral allyl alcohol compounds
US11358143B2 (en) 2019-03-19 2022-06-14 Siemens Healthcare Diagnostics Inc. Compositions, devices, and methods of mitigating lipoprotein interference in in vitro diagnostic assays for hydrophobic analytes

Family Cites Families (18)

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Publication number Priority date Publication date Assignee Title
US4594340A (en) 1984-11-29 1986-06-10 Hoffmann-La Roche Inc. 25,26-dehydro-1α,24R-dihydroxycholecalciferol and 25,26-dehydro-1α,24S-dihydroxycholecalciferol and the epimeric mixture
JPH07100685B2 (en) * 1985-08-02 1995-11-01 レオ・ファ−マシュ−ティカル・プロダクツ・リミテッド・エイ／エス（レ−ベンス・ケミスケ・ファブリック・プロデュクチオンスアクチ−セルスカブ） Novel vitamin D analog
DE3743824C2 (en) * 1987-12-23 1997-03-06 Hoechst Ag Process for the enzymatic resolution of racemic alcohols with / in vinyl esters by transesterification
US4996158A (en) * 1987-12-26 1991-02-26 Junichi Oda Optical resolution of racemic alcohols
US5401731A (en) 1989-06-29 1995-03-28 Leo Pharmaceutical Products Ltd. A/S (Lovens Kemiske Fabrik Productionsaktieselskab) Vitamin D analogues
DE3933034A1 (en) 1989-10-02 1991-04-11 Schering Ag 24-HOMO-VITAMIN-D DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF
DE69123402T2 (en) 1990-08-13 1997-04-03 Suntory Ltd Process for the production of optically active alpha-hydroxyalkene derivatives
AU1247592A (en) 1991-01-08 1992-08-17 Lunar Corporation Methods for preparation and use of 1alpha,24-dihydroxy vitamin d2
US5789397A (en) 1991-01-08 1998-08-04 Bone Care International, Inc. Methods for preparation and use of 1A,24(S)-dihydroxy vitamin D2
US5413935A (en) * 1991-04-24 1995-05-09 E. R. Squibb & Sons, Inc. Process for selecting an enantiomer of a hydroxy lactone using pseudomonas lipase
US6262283B1 (en) 1996-12-06 2001-07-17 Magainin Pharmaceuticals Inc. Stereoselective synthesis of 24-hydroxylated compounds useful for the preparation of aminosterols, vitamin D analogs, and other compounds
JPH11130711A (en) 1997-10-24 1999-05-18 Teijin Ltd Synthetic intermediate of 1α, 24,25-trihydroxyvitamin D3s and method for producing the same
US6531459B1 (en) 1997-12-17 2003-03-11 Schering Aktiengesellschaft Vitamin D derivatives with phosphorus atoms in the side chains
GB9908327D0 (en) 1999-04-12 1999-06-09 Chirotech Technology Ltd Process for the preparation of prostaglandin precursors
US6362350B1 (en) 1999-07-01 2002-03-26 Wisconsin Alumni Research Foundation Crystalline 1α, 24(S)-dihydroxyvitamin D2 and method of purification thereof
JP2001204484A (en) 2000-01-20 2001-07-31 Eisai Co Ltd Method for producing optically active substance using enzyme
NL1015313C2 (en) 2000-05-26 2001-11-27 Dsm Nv Process for the preparation of enantiomerically enriched esters and alcohols.
AU2003275987A1 (en) 2002-06-13 2003-12-31 Teva Pharmaceutical Industries Ltd. Epimerization of analogs of vitamin d

Also Published As

Publication number Publication date
KR100630859B1 (en) 2006-10-04
CN1639329A (en) 2005-07-13
HRP20040674A2 (en) 2005-06-30
EP1470220B1 (en) 2011-10-05
AU2003210473A1 (en) 2003-07-30
US8129173B2 (en) 2012-03-06
NO20043323L (en) 2004-08-10
IL162920A0 (en) 2005-11-20
MXPA04006741A (en) 2006-05-31
WO2003060094A3 (en) 2003-12-24
JP2005514929A (en) 2005-05-26
EP1470220A4 (en) 2007-12-05
PL373677A1 (en) 2005-09-05
EP1470220A2 (en) 2004-10-27
CA2472178A1 (en) 2003-07-24
IS7347A (en) 2004-07-07
KR20040081122A (en) 2004-09-20
US20030166226A1 (en) 2003-09-04
WO2003060094A2 (en) 2003-07-24

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